Polaroid Corporation

Jean B Rogers

James R Bartels-Keith

Eva R Karger

Mary T Burgess

James R Bartles-Keith

This invention relates to a method of synthesizing 3-amino-2-hydroxy-2-cyclopentenones possessing an aliphatic substituent in the 4-position which comprises reacting cyanoacetamide with an aliphatic aldehyde to yield the corresponding .beta.-substituted-.alpha.,.alpha.'-dicyanoglutaramide, hydrolyzing the amide to the corresponding .beta.-substituted glutaric acid, esterifying the acid to the corresponding dialkyl diester, converting the diester to a 1,2-bis(trimethylsiloxy)-4-substituted cyclopentene by reductive cyclization using chlorotrimethylsilane in the presence of sodium, hydrolyzing and oxidizing the bis(trimethylsiloxy) compound to the 2-hydroxy-4-substituted-2-cyclopentenone in the presence of a cupric salt, nitrosating the 2-cyclopentenone to the 2-hydroxy-4-substituted-5-oximino-2-cyclopentenone, converting the oxime to the 2-acetoxy-3-amino-4-substituted-2-cyclopentenone by reductive acetylation and removing the acetyl group by alkanolysis to yield the 3-amino-2-hydroxy-4-substituted-2-cyclopentenone product.

Synthesis of amino hydroxy cyclopentenones

This invention relates to N-nitroso compounds having the formula ##STR1## wherein R and R' each are selected from hydrogen and alkyl, Z is --CN or --COOR' wherein R' is alkyl and n is a positive integer from 1 to 7. These compounds are useful as intermediates in the preparation of photographic silver halide developing agents.

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Carlisle, MA, United States of America

Jean B Rogers